The prior art discloses the presence of C10, C11 and C12 alkatrienoic acids and ester and amide derivatives thereof in a wide variety of botanicals the use thereof to impart flavor and/or a tingling and/or warming sensations in the oral cavity and on skin when used in foodstuffs, chewing gum, oral care products, hair care products, colognes, topical cosmetic products or medicinal products. Such C10, C11 and C12 alkatrienoic acids and ester and amide derivatives thereof are also disclosed as exhibiting biological activity, most notably anti-bacterial, anti-fungal and insecticidal activity. The most significant compounds which are members of the genus: “C10, C11 and C12 alkatrienoic acids and ester and amide derivatives thereof” are those disclosed as follows:
(a) Amides:
Spilanthol or Affinin having the structure
the use of which in oral care, skin care and medicinal products is disclosed in Nakanatsu et al, Published European Patent Application EP 1,121,927 A2; the use of which as an oral sensate, flavor enhancer and potentiator is disclosed in U.S. Published Patent Application 2002/0122778 A1; and the pungency of which is disclosed in Nakatani et al “Pungent Alkamides from Spilanthes acmella L. var. oleracea Clarke, Biosci. Biotech. Biochem., 56(5), 759–762 (1992);
Isoaffinin having the structure:
disclosed in Gamboa-Leon et al., “Isobutylamide numbing agents of toothache grass”, Biochemical Systematics and Ecology 28 (2000) 1019–1021;
N-isobutyl E2, Z7, E9-undecatrienamide having the structure:
disclosed in Rameswak et al., “Bioactive N-isobutylamides from flower buds of Spilanthes acmella”, Phytochemistry 51 (1999) 729–732;
The disclosure of the compound having the structure:
by Snider et al., “Synthesis of the N-((1E)-Alkenyl)-(2Z,4Z)-heptadienamide Side Clain of Salicilihalamide A and Apicularens A and B”, Organic Letters (2000), Vol. 2, No. 3, pp. 407–408.(b) Acids:
The presence of dodecatrienoic acid (structure not specified) in a Hop Plant named “YCR Accession No. 14” having an aroma with sharp, floral and spicy notes, as disclosed in Zimmermann, U.S. Plant Patent PP12,213 P2;
The disclosure of the compound having the structure:
by Crombie, “Amides of Vegetable Origin, Part VII, Synthesis of N-isobutyldodeca-trans-2:trans-4:trans-8- and trans-2:trans-4:cis-8-trienamide and their relation to Sanshool I”, J. Chem. Soc. 1955, pp. 4244–4249.
Published application for U.S. Patent 2003/0068330 A1 published on Apr. 10, 2003 discloses 2,6,10-dodecatrienoic acid (without specifying any particular isomer thereof) for potentiating the activity of Nerve Growth Factor (NGF).
(c) Esters:
The disclosure of the compound having the structure:
by Furber et al., “Stereospecific Diene Synthesis using Acetylene Carbocupration; Preparation of Navel Orangeworm Pheremone and Leukotriene Analogues”, J. Chem. Soc. Perkin Trans. I, 1986, pp. 1809–1815;
The disclosure of the compound having the structure:
by Tanaka et al., “Structure and Synthesis of a New Hypotensive Vasodilator Isolated from Streptomyces Aureofaciens”, Tetrahedron Letters, Vol. 22, No. 35, pp. 3421–3422, 1981.
Despite the existence in the prior art and in commerce of such a vast number of C10, C11 and C12 alkatrienoic acids and ester and amide derivatives thereof, there is an increasing ongoing need for flavor ingredients, skin care ingredients, oral care ingredients and hair care ingredients that exhibit organoleptically-acceptable somatosensory activity or flavor property, particularly at relatively low threshold levels.